First, as
@nicho said, Apple control the hardware. Microsoft
can't say 'As of 2021 all new PCs will be ARM based' - Apple
can and
has successfully done the equivalent
twice in the past. Windows has always been tied to incremental improvements of the same old 8086 processor. Remember Windows for PowerPC, Alpha, MIPS, Itanium, ARM (at least 1 previous attempt)... they went well.
Second, Apple doesn't have
anything like the same legacy software issue.
A couple of weeks ago I had a query about some software I wrote in the 1990s - I fired up Windows 10 (32 bit edition - still supported) , dug out a binary, double clicked and - bingo! Ran perfectly except it was a tad 'soft focus' on a 4k screen. Tried another, more complex one with DLL back-end and stuff - worked fine. 20+ year-old binaries running 'out of the box' - t
hat's the expectation, nay requirement, of the huge corporate PC-using sector on which MS relies. On a modern Mac, you're lucky if a 5-year-old binary will run, and 20-year-old software would need a major re-write from 'classic' to 64-bit OS X Cocoa. There just isn't the same expectation/reliance on old apps as in the PC world.
You've got your facts mixed up.
Classic (10.0 -10.4) was a compatibility layer that let Mac OS 9 and earlier code run on Mac OS X. It was written for PPC but since it could run the 'classic' 68k emulator it also worked with 68k apps.
68k emulator (7.1.2 to 9.2.2, then as part of 'classic') was an emulator that let 68k code run on PPC.
Rosetta (10.4-10.7) was an emulator (or, more precisely, a binary translator) that let PPC code run on Intel.
Both the 68k-PPC and PPC-to-x86 transitions went exactly the same way: long-term, developers had to re-compile their apps for the new processor and ship 'Fat Binaries/Universal binaries' containing both versions, but as an interim solution, and last resort for 'abandonware', there was an emulator available, which Apple supported for as long as practicable. There's every reason to believe that the rumoured ARM transition would go the same way (an x86-64 emulator/translator for ARM is a lawyer problem, not a technical one).
...and for the vast majority of code, making a Universal Binary is a matter of checking a box in XCode and re-compiling your processor-independent C/ObjC/C++/Swift code. Know what is
not fun? Writing assembly code or other CPU-specific code
at all so developers only do it when absolutely necessary - even things like drivers can be substantially written in C.
In fact, the 68k-to-PPC and PPC-x86 transitions
had it worse - the older and slower the processor and the less sophisticated the OS in terms of abstracted graphics/sound/acceleration frameworks the more likely developers are to resort to assembly language or other hardware-dependent code. Then the PPC-to-x86 transition meant switching from big- to little-endian mode (the order in which bytes are stored in 16-bit or longer numbers) which can impact on data and file formats even in high-level languages. The switch to 64 bit - now done - will have been a bigger deal for many applications than switching from one 64-bit/little-endian CPU (x86-64) to another (arm64).
The Mac OS Classic to Mac OS X transition was a different - and far more impactful - change to a completely different, non-source-code-compatible OS that required
all applications to be significantly re-written. The 'carbon' interim application framework helped avoid having to re-write UI-code from scratch but it certainly wasn't 'tick box' - in fact, for many, it was 'learn a whole new set of developer tools' (Metrowerks->XCode).
Basically, any application that has made it through 3/4 such 'extinction events' should be in pretty good shape to switch to ARM with modest effort, and newer software written to Apple's modern guidelines should be a breeze. Yes, of course, there will be exceptions (esp. with obscure pro-app plugins) but all this has happened before and can happen again.
The one fly in the ointment this time round, that didn't exist before, are the users who rely on virtualising or 'bootcamping' x86 operating systems. That may be a sacrifice that Apple is prepared to make...
Sure - its just a rumour. Nothing is certain. That doesn't make re-heating the same discredited arguments that were used against the PPC and Intel switches valid.